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Identification
NameErgocalciferol
Accession NumberDB00153  (NUTR00005, APRD00426)
TypeSmall Molecule
GroupsApproved, Nutraceutical
Description

Ergocalciferol (Vitamin D2) is a derivative of ergosterol formed by ultraviolet rays breaking of the C9-C10 bond. It differs from cholecalciferol in having a double bond between C22 and C23 and a methyl group at C24. [PubChem]

Structure
Thumb
Synonyms
(3beta,5Z,7e,22e)-9,10-Secoergosta-5,7,10(19),22-tetraen-3-ol
(5Z,7e,22e)-(3S)-9,10-Seco-5,7,10(19),22-ergostatetraen-3-ol
(5Z,7e,22e)-(3S)-9,10-Secoergosta-5,7,10(19),22-tetraen-3-ol
Activated ergosterol
Calciferol
Ercalciol
Ergocalciferol
Ergocalciferolum
Oleovitamin D2
Viosterol
Vitamin D2
Vitamina D2
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
D-fortecapsule50000 unitoralEuro Pharm International Canada Inc1999-12-30Not applicableCanada
Drisdolcapsule, liquid filled1.25 mg/1oralSanofi Aventis U.S. Llc1974-11-11Not applicableUs
Ergocalciferolcapsule, liquid filled1.25 mg/1oralWinthrop U.S.2009-11-10Not applicableUs
Osto-D2capsule50000 unitoralPaladin Labs Inc2008-02-08Not applicableCanada
Radiostol Cap 50000iucapsule50000 unitoralAllen & Hanburys A Glaxo Canada Ltd. Co.1989-12-151996-09-10Canada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Ergocalciferolcapsule1.25 mg/1oralPhysicians Total Care, Inc.2007-07-12Not applicableUs
Ergocalciferolcapsule1.25 mg/1oralBlenheim Pharmacal, Inc.2013-10-02Not applicableUs
Ergocalciferolcapsule, liquid filled1.25 mg/1oralClinical Solutions Wholesale2010-07-23Not applicableUs
Ergocalciferolcapsule1.25 mg/1oralPd Rx Pharmaceuticals, Inc.2009-08-17Not applicableUs
Ergocalciferolcapsule, liquid filled1.25 mg/1oralReady Meds2010-07-23Not applicableUs
Ergocalciferolcapsule, liquid filled1.25 mg/1oralSigma Pharm Laboratories, Llc2012-01-28Not applicableUs
Ergocalciferolcapsule1.25 mg/1oralbryant ranch prepack2009-08-17Not applicableUs
Ergocalciferolcapsule1.25 mg/1oralBreckenridge Pharmaceutical, Inc.2009-08-17Not applicableUs
Ergocalciferolcapsule, liquid filled1.25 mg/1oralCarilion Materials Management2010-07-23Not applicableUs
Ergocalciferolcapsule, liquid filled1.25 mg/1oralAv Kare, Inc.2012-06-052016-02-04Us
Ergocalciferolcapsule, liquid filled1.25 mg/1oralUnit Dose Services2010-07-23Not applicableUs
Ergocalciferolcapsule1.25 mg/1oralAmerican Health Packaging2011-01-07Not applicableUs
Ergocalciferolcapsule, liquid filled1.25 mg/1oralAv Kare, Inc.2015-07-23Not applicableUs
Ergocalciferolcapsule, liquid filled1.25 mg/1oralProficient Rx LP2010-07-23Not applicableUs
Ergocalciferolcapsule1.25 mg/1oralPliva Inc.2002-06-01Not applicableUs
Ergocalciferolcapsule1.25 mg/1oralDispensing Solutions, Inc.2009-08-17Not applicableUs
Ergocalciferolcapsule1.25 mg/1oralLake Erie Medical DBA Quality Care Products LLC2009-08-17Not applicableUs
Ergocalciferolcapsule1.25 mg/1oralSt Marys Medical Park Pharmacy2014-05-22Not applicableUs
Ergocalciferolcapsule, liquid filled1.25 mg/1oralRising Pharamceuticals, Inc2010-07-23Not applicableUs
Ergocalciferolcapsule, liquid filled1.25 mg/1oralBanner Life Sciences Llc.2015-06-01Not applicableUs
Ergocalciferolcapsule1.25 mg/1oralAidarex Pharmaceuticals LLC2009-08-17Not applicableUs
Ergocalciferolcapsule1.25 mg/1oralGolden State Medical Supply, Inc.2009-08-17Not applicableUs
Vitamin Dcapsule1.25 1/1oralAvera Mc Kennan Hospital2015-03-13Not applicableUs
Vitamin Dcapsule, liquid filled1.25 mg/1oralPaddock Laboratories, LLC2009-12-152015-11-30Us
Vitamin Dcapsule1.25 mg/1oralA S Medication Solutions Llc2010-03-15Not applicableUs
Vitamin Dcapsule1.25 mg/1oralPreferred Pharmaceuticals, Inc.2015-02-23Not applicableUs
Vitamin Dcapsule1.25 1/1oralProficient Rx LP2014-05-16Not applicableUs
Vitamin Dcapsule1.25 mg/1oralPreferred Pharmaceuticals Inc.2016-04-12Not applicableUs
Vitamin Dcapsule1.25 mg/1oralAphena Pharma Solutions Tennessee, Llc2010-03-15Not applicableUs
Vitamin Dcapsule1.25 mg/1oralSun Pharmaceutical Industries, Inc.2010-03-15Not applicableUs
Vitamin Dcapsule1.25 1/1oralREMEDYREPACK INC.2016-02-09Not applicableUs
Vitamin Dcapsule1.25 1/1oralStrides Arcolab Limited2014-05-16Not applicableUs
Vitamin Dcapsule1.25 mg/1oralPd Rx Pharmaceuticals, Inc.2010-03-15Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
CalcidolNot Available
DeltalinNot Available
Brand mixtures
NameLabellerIngredients
Aquasol A & D DropsRhone Poulenc Rorer Consumer Inc.
Cal/mag 2:1 With DWn Pharmaceuticals Ltd.
Calcium Mg and Zn Capsules With Vitamin DRheingold Food International Ltd.
Calcium Chelate Plus Vit DHall Laboratories, Ltd.
Calcium Citrate W Vitamin D TabNutri Dyn Products Ltd.
Calcium Magnesium 2:1 Tablets With Vitamin DSisu Inc.
Calcium Magnesium Avec Vitamine D Et ZincLes Aliments Nutri Source Inc.
Calcium Magnesium Plus Vitamin D LiquidJamp Pharma Corporation
Calcium With Vitamin D2Sisu Inc.
Calcium With Vitamins C and D TabPure Life International Prods Inc.
Children Pediatric Vitamins DropsStanley Pharmaceuticals, A Division Of Vita Health Products Inc.
Childrens Chewable Multiple Vitamins TabPharmavite Llc
Formula CmNutrivention Nutritional Products
Formula JsNutrivention Nutritional Products
Infant's Multiple Vitamin DropsStanley Pharmaceuticals, A Division Of Vita Health Products Inc.
Infants' Vitamin DropsKsl Pharmaceuticals
Insur-all Vitamin SupplementGarden State Nutritionals
Kanga-V Multivitamins & MineralsLacombe Drugs (1992) Ltd
Kenwood Liquid SupplementKenwood Laboratories (Division Of Bradley Pharmaceuticals)
M.V.I. PediatricHospira Worldwide, Inc.
Maxi 10 TabDesbergers LtÉe, Division Of Technilab Inc.
Maxi 6 LiqDesbergers LtÉe, Division Of Technilab Inc.
Multiple Vitamin Plus Minerals TabHall Laboratories, Ltd.
Multiple VitaminsStanley Pharmaceuticals, A Division Of Vita Health Products Inc.
Multiple Vitamins With IronStanley Pharmaceuticals, A Division Of Vita Health Products Inc.
One A Day TabCountry Health Laboratories Ltd.
Paramettes SyrupWyeth Ayerst Canada Inc.
Sopalamine/3b Plus CTechnilab Pharma Inc.
Tender Age Multi VitaminsJamieson Laboratories Ltd
Vitamines Pour Bebes Et EnfantsHerbes Universelles Inc.
Zoo ChewsHall Laboratories, Ltd.
SaltsNot Available
Categories
UNIIVS041H42XC
CAS number50-14-6
WeightAverage: 396.6484
Monoisotopic: 396.33921603
Chemical FormulaC28H44O
InChI KeyInChIKey=MECHNRXZTMCUDQ-RKHKHRCZSA-N
InChI
InChI=1S/C28H44O/c1-19(2)20(3)9-10-22(5)26-15-16-27-23(8-7-17-28(26,27)6)12-13-24-18-25(29)14-11-21(24)4/h9-10,12-13,19-20,22,25-27,29H,4,7-8,11,14-18H2,1-3,5-6H3/b10-9+,23-12+,24-13-/t20-,22+,25-,26+,27-,28+/m0/s1
IUPAC Name
(1S,3Z)-3-{2-[(1R,3aS,4E,7aR)-1-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexan-1-ol
SMILES
CC(C)[C@@H](C)\C=C\[C@@H](C)[C@@]1([H])CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)CCC1=C
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing 8 isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentTriterpenoids
Alternative Parents
Substituents
  • Polycyclic triterpenoid
  • Triterpenoid
  • Steroid
  • Cyclohexanol
  • Cyclic alcohol
  • Secondary alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Pharmacology
IndicationFor use in the management of hypocalcemia and its clinical manifestations in patients with hypoparathyroidism, as well as for the treatment of familial hypophosphatemia (vitamin D resistant rickets). This drug has also been used in the treatment of nutritional rickets or osteomalacia, vitamin D dependent rickets, rickets or osteomalacia secondary to long-term high dose anticonvulsant therapy, early renal osteodystrophy, osteoporosis (in conjunction with calcium), and hypophosphatemia associated with Fanconi syndrome (with treatment of acidosis).
PharmacodynamicsErgoalcifediol (Vitamin D2) is a fat soluble steroid hormone precursor of vitamin D. The principal biologic function of vitamin D is the maintenance of normal levels of serum calcium and phosphorus in the bloodstream by enhancing the efficacy of the small intestine to absorb these minerals from the diet. Cholecalciferol is synthesized within our bodies naturally, but if UV exposure is inadequate or the metabolism of cholecalciferol is abnormal, then an exogenous source is required. Vitamin D2 is converted to 25-hydroxyvitamin D (25OHD) in the liver, and then to the active form, 1,25-dihydroxyvitamin D (1,25(OH)2D), in the kidney. Once transformed, it binds to the vitamin D receptor, which leads to a variety of regulatory roles. Vitamin D plays an important role in maintaining calcium balance and in the regulation of parathyroid hormone (PTH). It promotes renal reabsorption of calcium, increases intestinal absorption of calcium and phosphorus, and increases calcium and phosphorus mobilization from bone to plasma. Very few foods naturally contain vitamin D. Sources that contain the vitamin include fatty fish, the liver and fat of aquatic mammals (e.g., seals, polar bears), and eggs from chickens fed vitamin D-fortified feed. As such, many countries have instituted policies to fortify certain foods with vitamin D to compensate for the potentially low exposures of skin to sunlight. Vitamin D deficiency results in inadequate mineralization of bone or compensatory skeletal demineralization and causes decreased ionized calcium concentrations in blood and a resultant increase in the production and secretion of PTH. Increase in PTH stimulates the mobilization of skeletal calcium, inhibits renal excretion of calcium, and stimulates renal excretion of phosphorus. This results in normal fasting serum calcium concentrations and low or near-normal serum phosphorus. The enhanced mobilization of skeletal calcium induced by this secondary hyperparathyroidism leads porotic bone.
Mechanism of actionActivated ergocalciferol increases serum calcium and phosphate concentrations, primarily by increasing intestinal absorption of calcium and phosphate through binding to a specific receptor in the mucosal cytoplasm of the intestine. Subsequently, calcium is absorbed through formation of a calcium-binding protein. 25-hydroxyergocalciferol is the intermediary metabolite of ergocalciferol. Although this metabolite exhibits 2–5 times more activity than unactivated ergocalciferol in curing rickets and inducing calcium absorption and mobilization (from bone) in animals, this increased activity is still insufficient to affect these functions at physiologic concentrations. Activated ergocalciferol stimulate resorption of bone and are required for normal mineralization of bone. Physiological doses of ergocalciferol also promotes calcium reabsorption by the kidneys, but the significance of this effect is not known.
Related Articles
AbsorptionReadily absorbed from small intestine (proximal or distal), requires presence of bile salts.
Volume of distributionNot Available
Protein binding>99.8%
Metabolism

Within the liver, ergocalciferol is hydroxylated to ercalcidiol (25-hydroxyergocalciferol) by the enzyme 25-hydroxylase. Within the kidney, ercalcidiol serves as a substrate for 1-alpha-hydroxylase, yielding ercalcitriol (1,25-dihydroxyergocalciferol), the biologically active form of vitamin D2.

SubstrateEnzymesProduct
Ergocalciferol
Not Available
25-Hydroxyvitamin D2-25-glucuronideDetails
Ergocalciferol
Not Available
Vitamin D2 3-glucuronideDetails
Ergocalciferol
Not Available
25-Hydroxyvitamin D2 25-(beta-glucuronide)Details
Route of eliminationNot Available
Half life19 to 48 hours (however, stored in fat deposits in body for prolonged periods).
ClearanceNot Available
ToxicityLD50 = 23.7 mg/kg (Orally in mice); LD50 = 10 mg/kg (Orally in rats ); Nausea, vomiting and diarrhea, weight loss, irritability, weakness, fatigue, lassitude, and headache.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9428
Caco-2 permeable+0.8323
P-glycoprotein substrateSubstrate0.6628
P-glycoprotein inhibitor IInhibitor0.7614
P-glycoprotein inhibitor IINon-inhibitor0.8391
Renal organic cation transporterNon-inhibitor0.796
CYP450 2C9 substrateNon-substrate0.8432
CYP450 2D6 substrateNon-substrate0.9003
CYP450 3A4 substrateSubstrate0.7362
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.8924
CYP450 2D6 inhibitorNon-inhibitor0.9519
CYP450 2C19 inhibitorNon-inhibitor0.8784
CYP450 3A4 inhibitorNon-inhibitor0.8142
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8163
Ames testNon AMES toxic0.9401
CarcinogenicityNon-carcinogens0.9169
BiodegradationNot ready biodegradable0.9742
Rat acute toxicity3.6931 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8502
hERG inhibition (predictor II)Non-inhibitor0.7513
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Eli lilly and co
  • Sanofi aventis us llc
  • Orit laboratories llc
  • Sigmapharm laboratories llc
  • Strides arcolab ltd
  • Sun pharmaceutical industries inc
  • Banner pharmacaps inc
  • Chase chemical co lp
  • Everylife
  • Impax laboratories inc
  • Lannett co inc
  • Vitarine pharmaceuticals inc
  • West ward pharmaceutical corp
Packagers
Dosage forms
FormRouteStrength
Dropsoral
Capsuleoral
Tabletoral
Capsuleoral50000 unit
Capsule, liquid filledoral1.25 mg/1
Capsuleoral1.25 mg/1
Tablet (effervescent)oral
Injection, powder, lyophilized, for solutionintravenous
Syruporal
Capsuleoral1.25 1/1
Liquidoral
Prices
Unit descriptionCostUnit
Ergocalciferol powder234.4USD g
Doral 15 mg tablet3.41USD tablet
Doral 7.5 mg tablet3.37USD tablet
Drisdol 50000 unit capsule2.34USD capsule
Drisdol 8288 unit/ml Liquid0.48USD ml
Vitamin d 400 unit softgel0.04USD softgel capsule
Longs vitamin d 400 unit tablet0.03USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point116.5 °CPhysProp
water solubility50 mg/LTOMLIN,C (1994)
logP7.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.000433 mg/mLALOGPS
logP7.59ALOGPS
logP7.05ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)18.38ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity128.89 m3·mol-1ChemAxon
Polarizability50.73 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (9.78 KB)
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-003u-3911000000-dba9e396497310b31715View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0002-0129000000-77bd32807ec8ea97183bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0601-5902000000-ae4a4363ac10f9f0feb7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-05mo-9800000000-1ea9f4fa17117a9e6515View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-01ot-9801000000-17d2120d47f9c718ea95View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
Synthesis Reference

Charles W. Bishop, Glenville Jones, Ronald L. Horst, Nicholas J. Koszewski, Joyce C. Knutson, Raju Penmasta, Robert M. Moriarty, Stephen Strugnell, Timothy A. Reinhardt, Liang Guo, Sanjay K. Singhal, Lei Zhao, “Methods for preparation and use of 1A,24(S)-dihydroxy vitamin D2.” U.S. Patent US5789397, issued March, 1992.

US5789397
General References
  1. DeLuca HF: Overview of general physiologic features and functions of vitamin D. Am J Clin Nutr. 2004 Dec;80(6 Suppl):1689S-96S. [PubMed:15585789 ]
External Links
ATC CodesA11CC01
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (78.4 KB)
Interactions
Drug Interactions
Drug
AcenocoumarolErgocalciferol may decrease the anticoagulant activities of Acenocoumarol.
Aluminum hydroxideThe serum concentration of Aluminum hydroxide can be increased when it is combined with Ergocalciferol.
AminophyllineThe serum concentration of Aminophylline can be increased when it is combined with Ergocalciferol.
ColesevelamThe serum concentration of Ergocalciferol can be decreased when it is combined with Colesevelam.
DanazolDanazol may increase the hypercalcemic activities of Ergocalciferol.
DigoxinErgocalciferol may increase the arrhythmogenic activities of Digoxin.
DihydrotachysterolThe risk or severity of adverse effects can be increased when Dihydrotachysterol is combined with Ergocalciferol.
Mineral oilThe serum concentration of Ergocalciferol can be decreased when it is combined with Mineral oil.
OrlistatThe serum concentration of Ergocalciferol can be decreased when it is combined with Orlistat.
SucralfateThe serum concentration of Sucralfate can be increased when it is combined with Ergocalciferol.
TheophyllineThe serum concentration of Theophylline can be increased when it is combined with Ergocalciferol.
TrichlormethiazideTrichlormethiazide may increase the hypercalcemic activities of Ergocalciferol.
WarfarinErgocalciferol may decrease the anticoagulant activities of Warfarin.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Zinc ion binding
Specific Function:
Nuclear hormone receptor. Transcription factor that mediates the action of vitamin D3 by controlling the expression of hormone sensitive genes. Recruited to promoters via its interaction with BAZ1B/WSTF which mediates the interaction with acetylated histones, an essential step for VDR-promoter association. Plays a central role in calcium homeostasis.
Gene Name:
VDR
Uniprot ID:
P11473
Molecular Weight:
48288.64 Da
References
  1. Carvallo L, Henriquez B, Olate J, van Wijnen AJ, Lian JB, Stein GS, Onate S, Stein JL, Montecino M: The 1alpha,25-dihydroxy Vitamin D3 receptor preferentially recruits the coactivator SRC-1 during up-regulation of the osteocalcin gene. J Steroid Biochem Mol Biol. 2007 Mar;103(3-5):420-4. Epub 2007 Jan 10. [PubMed:17218095 ]
  2. Liu W, Tretiakova M, Kong J, Turkyilmaz M, Li YC, Krausz T: Expression of vitamin D3 receptor in kidney tumors. Hum Pathol. 2006 Oct;37(10):1268-78. Epub 2006 Jul 27. [PubMed:16949927 ]
  3. Ewing AK, Attner M, Chakravarti D: Novel regulatory role for human Acf1 in transcriptional repression of vitamin D3 receptor-regulated genes. Mol Endocrinol. 2007 Aug;21(8):1791-806. Epub 2007 May 22. [PubMed:17519354 ]
  4. Gallagher JC, Sai AJ: Vitamin D insufficiency, deficiency, and bone health. J Clin Endocrinol Metab. 2010 Jun;95(6):2630-3. doi: 10.1210/jc.2010-0918. [PubMed:20525913 ]
  5. Straube S, Derry S, Moore RA, McQuay HJ: Vitamin D for the treatment of chronic painful conditions in adults. Cochrane Database Syst Rev. 2010 Jan 20;(1):CD007771. doi: 10.1002/14651858.CD007771.pub2. [PubMed:20091647 ]
  6. Jurutka PW, Bartik L, Whitfield GK, Mathern DR, Barthel TK, Gurevich M, Hsieh JC, Kaczmarska M, Haussler CA, Haussler MR: Vitamin D receptor: key roles in bone mineral pathophysiology, molecular mechanism of action, and novel nutritional ligands. J Bone Miner Res. 2007 Dec;22 Suppl 2:V2-10. doi: 10.1359/jbmr.07s216. [PubMed:18290715 ]
  7. Mikhak B, Hunter DJ, Spiegelman D, Platz EA, Hollis BW, Giovannucci E: Vitamin D receptor (VDR) gene polymorphisms and haplotypes, interactions with plasma 25-hydroxyvitamin D and 1,25-dihydroxyvitamin D, and prostate cancer risk. Prostate. 2007 Jun 15;67(9):911-23. [PubMed:17440943 ]
  8. Marks HD, Fleet JC, Peleg S: Transgenic expression of the human Vitamin D receptor (hVDR) in the duodenum of VDR-null mice attenuates the age-dependent decline in calcium absorption. J Steroid Biochem Mol Biol. 2007 Mar;103(3-5):513-6. Epub 2007 Jan 5. [PubMed:17207992 ]
  9. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Oxidoreductase activity
Specific Function:
Has a role in maintaining calcium homeostasis. Catalyzes the NADPH-dependent 24-hydroxylation of calcidiol (25-hydroxyvitamin D(3)) and calcitriol (1-alpha,25-dihydroxyvitamin D(3)). The enzyme can perform up to 6 rounds of hydroxylation of calcitriol leading to calcitroic acid. It also shows 23-hydroxylating activity leading to 1-alpha,25-dihydroxyvitamin D(3)-26,23-lactone as end product.
Gene Name:
CYP24A1
Uniprot ID:
Q07973
Molecular Weight:
58874.695 Da
References
  1. Masuda S, Strugnell SA, Knutson JC, St-Arnaud R, Jones G: Evidence for the activation of 1alpha-hydroxyvitamin D2 by 25-hydroxyvitamin D-24-hydroxylase: delineation of pathways involving 1alpha,24-dihydroxyvitamin D2 and 1alpha,25-dihydroxyvitamin D2. Biochim Biophys Acta. 2006 Feb;1761(2):221-34. Epub 2006 Feb 2. [PubMed:16516540 ]
  2. Sakaki T, Kagawa N, Yamamoto K, Inouye K: Metabolism of vitamin D3 by cytochromes P450. Front Biosci. 2005 Jan 1;10:119-34. Print 2005 Jan 1. [PubMed:15574355 ]
  3. Abe D, Sakaki T, Kusudo T, Kittaka A, Saito N, Suhara Y, Fujishima T, Takayama H, Hamamoto H, Kamakura M, Ohta M, Inouye K: Metabolism of 2 alpha-propoxy-1 alpha,25-dihydroxyvitamin D3 and 2 alpha-(3-hydroxypropoxy)-1 alpha,25-dihydroxyvitamin D3 by human CYP27A1 and CYP24A1. Drug Metab Dispos. 2005 Jun;33(6):778-84. Epub 2005 Mar 11. [PubMed:15764712 ]
  4. Sakaki T: [Recent studies on vitamin D metabolizing enzymes]. Clin Calcium. 2006 Jul;16(7):1129-35. [PubMed:16816472 ]
  5. Inouye K, Sakaki T: Enzymatic studies on the key enzymes of vitamin D metabolism; 1 alpha-hydroxylase (CYP27B1) and 24-hydroxylase (CYP24). Biotechnol Annu Rev. 2001;7:179-94. [PubMed:11686044 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Iron ion binding
Specific Function:
Catalyzes the conversion of 25-hydroxyvitamin D3 (25(OH)D) to 1-alpha,25-dihydroxyvitamin D3 (1,25(OH)2D) plays an important role in normal bone growth, calcium metabolism, and tissue differentiation.
Gene Name:
CYP27B1
Uniprot ID:
O15528
Molecular Weight:
56503.475 Da
References
  1. Turunen MM, Dunlop TW, Carlberg C, Vaisanen S: Selective use of multiple vitamin D response elements underlies the 1 alpha,25-dihydroxyvitamin D3-mediated negative regulation of the human CYP27B1 gene. Nucleic Acids Res. 2007;35(8):2734-47. Epub 2007 Apr 10. [PubMed:17426122 ]
  2. Gallagher JC, Sai AJ: Vitamin D insufficiency, deficiency, and bone health. J Clin Endocrinol Metab. 2010 Jun;95(6):2630-3. doi: 10.1210/jc.2010-0918. [PubMed:20525913 ]
  3. Sakaki T, Kagawa N, Yamamoto K, Inouye K: Metabolism of vitamin D3 by cytochromes P450. Front Biosci. 2005 Jan 1;10:119-34. Print 2005 Jan 1. [PubMed:15574355 ]
  4. Sakaki T: [Recent studies on vitamin D metabolizing enzymes]. Clin Calcium. 2006 Jul;16(7):1129-35. [PubMed:16816472 ]
  5. Inouye K, Sakaki T: Enzymatic studies on the key enzymes of vitamin D metabolism; 1 alpha-hydroxylase (CYP27B1) and 24-hydroxylase (CYP24). Biotechnol Annu Rev. 2001;7:179-94. [PubMed:11686044 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Catalyzes the first step in the oxidation of the side chain of sterol intermediates; the 27-hydroxylation of 5-beta-cholestane-3-alpha,7-alpha,12-alpha-triol. Has also a vitamin D3-25-hydroxylase activity.
Gene Name:
CYP27A1
Uniprot ID:
Q02318
Molecular Weight:
60234.28 Da
References
  1. Binkley N, Ramamurthy R, Krueger D: Low vitamin D status: definition, prevalence, consequences, and correction. Endocrinol Metab Clin North Am. 2010 Jun;39(2):287-301, table of contents. doi: 10.1016/j.ecl.2010.02.008. [PubMed:20511052 ]
  2. Masuda S, Strugnell SA, Knutson JC, St-Arnaud R, Jones G: Evidence for the activation of 1alpha-hydroxyvitamin D2 by 25-hydroxyvitamin D-24-hydroxylase: delineation of pathways involving 1alpha,24-dihydroxyvitamin D2 and 1alpha,25-dihydroxyvitamin D2. Biochim Biophys Acta. 2006 Feb;1761(2):221-34. Epub 2006 Feb 2. [PubMed:16516540 ]
  3. Sakaki T, Kagawa N, Yamamoto K, Inouye K: Metabolism of vitamin D3 by cytochromes P450. Front Biosci. 2005 Jan 1;10:119-34. Print 2005 Jan 1. [PubMed:15574355 ]
  4. Abe D, Sakaki T, Kusudo T, Kittaka A, Saito N, Suhara Y, Fujishima T, Takayama H, Hamamoto H, Kamakura M, Ohta M, Inouye K: Metabolism of 2 alpha-propoxy-1 alpha,25-dihydroxyvitamin D3 and 2 alpha-(3-hydroxypropoxy)-1 alpha,25-dihydroxyvitamin D3 by human CYP27A1 and CYP24A1. Drug Metab Dispos. 2005 Jun;33(6):778-84. Epub 2005 Mar 11. [PubMed:15764712 ]
  5. Sakaki T: [Recent studies on vitamin D metabolizing enzymes]. Clin Calcium. 2006 Jul;16(7):1129-35. [PubMed:16816472 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. Binkley N, Ramamurthy R, Krueger D: Low vitamin D status: definition, prevalence, consequences, and correction. Endocrinol Metab Clin North Am. 2010 Jun;39(2):287-301, table of contents. doi: 10.1016/j.ecl.2010.02.008. [PubMed:20511052 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Has a D-25-hydroxylase activity on both forms of vitamin D, vitamin D(2) and D(3).
Gene Name:
CYP2R1
Uniprot ID:
Q6VVX0
Molecular Weight:
57358.82 Da
References
  1. Ramos-Lopez E, Bruck P, Jansen T, Pfeilschifter JM, Radeke HH, Badenhoop K: CYP2R1-, CYP27B1- and CYP24-mRNA expression in German type 1 diabetes patients. J Steroid Biochem Mol Biol. 2007 Mar;103(3-5):807-10. Epub 2007 Jan 16. [PubMed:17223345 ]
  2. Ramos-Lopez E, Bruck P, Jansen T, Herwig J, Badenhoop K: CYP2R1 (vitamin D 25-hydroxylase) gene is associated with susceptibility to type 1 diabetes and vitamin D levels in Germans. Diabetes Metab Res Rev. 2007 Nov;23(8):631-6. [PubMed:17607662 ]
  3. Masuda S, Strugnell SA, Knutson JC, St-Arnaud R, Jones G: Evidence for the activation of 1alpha-hydroxyvitamin D2 by 25-hydroxyvitamin D-24-hydroxylase: delineation of pathways involving 1alpha,24-dihydroxyvitamin D2 and 1alpha,25-dihydroxyvitamin D2. Biochim Biophys Acta. 2006 Feb;1761(2):221-34. Epub 2006 Feb 2. [PubMed:16516540 ]
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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:08